THE SYNTHESIS OF 3,4-H-2(2)-3Z-HEXENAL AND 6,6,6-H-2(3)-3Z-HEXENAL

6,6,6-H-2(3)-3Z-Hexenal (3b) has been prepared in 89% yield and in greater than 94% purity by the oxidation of 6,6,6-H-2(3)-3Z-Hexen-1-ol (2b) with the Dess/Martin periodinane (1) in fluorotrichloromethane (freon 11), Use of the freon solvent greatly improved the recovery of this volatile aldehyde, Similarly the oxidation of 3,4-H-2(2)-3Z-hexen-1-ol (5) yielded 3,4-H-2(2)-3Z-hexenal (6) in a 92% isolated yield with a purity of greater than 99%. 3,4-H-2(2)-3Z-Hexen-1-ol (5) was prepared in 87% by the catalytic deuterogenation of 3-hexyn-1-ol (4) in an improved synthetic procedure.